Dempsey took the tie to extra-time with just eight minutes of normal time remaining - but Tottenham's task was then made much harder by the injury-time dismissal of Jan Vertonghen.

Basel threw everything at the Londoners in extra-time, but they could not find a way through and the game went to penalties.

Tottenham had not won a penalty shoot-out since 1994 - and it showed.

Tom Huddlestone and Emmanuel Adebayor both missed from the spot while Basel converted all four of their efforts to send Andre Villas-Boas' team crashing out of the competition.

Despite their hard work tonight on a ground where Bayern Munich and Manchester United were defeated last year, a dramatic run that has included red cards, an off the pitch stabbing, racist chanting, and two last-gasp wins, has now ended.

Villas-Boas can be proud of his squad's endeavours - but they would have not been in this situation tonight had they wilted so pitifully in last week's first leg.

It also remains to be seen whether the Portuguese's policy of playing his best players in the search of his second European trophy in three seasons has been a wise one with Tottenham's patched-up squad currently faltering in the home straight in the league.

The hosts were much more effective on the attack in the sold-out stadium on the banks of the Rhine.

Brad Friedel watched nervously as Fabian Schar's free-kick drifted just wide and Salah then found space in the box but shot over.

Basel dropped deep in an attempt to keep Spurs' attack at bay. It would take something special to breach their two rigid banks of four, and that was exactly what Jan Vertonghen produced in the 23rd minute.

The Belgian sliced open the Basel defence with a pass that left Dragovic flat on his backside and Dempsey rounded the goalkeeper before slotting in to an empty net.

Villas-Boas jumped for joy - but he was soon cursing his luck after Mousa Dembele's error allowed Basel to level.

Mohamed El-Nenny intercepted a sloppy pass from the midfielder and worked the ball out wide to Marco Streller, who cut open the Spurs defence to find Salah - who poked the ball past Friedel.

A series of flares went off in the home end and the away side went in to panic mode, giving the ball away easily.